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WO2009124627A1 - Dérivés du fluor pour dispositifs électroluminescents organiques - Google Patents

Dérivés du fluor pour dispositifs électroluminescents organiques Download PDF

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Publication number
WO2009124627A1
WO2009124627A1 PCT/EP2009/001736 EP2009001736W WO2009124627A1 WO 2009124627 A1 WO2009124627 A1 WO 2009124627A1 EP 2009001736 W EP2009001736 W EP 2009001736W WO 2009124627 A1 WO2009124627 A1 WO 2009124627A1
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Prior art keywords
formula
aromatic
compounds
substituted
groups
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PCT/EP2009/001736
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German (de)
English (en)
Inventor
Philipp Stoessel
Holger Heil
Dominik Joosten
Christof Pflumm
Anja Gerhard
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Merck Patent GmbH
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Merck Patent GmbH
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Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to EP09730490A priority Critical patent/EP2260023B1/fr
Priority to US12/936,644 priority patent/US8361638B2/en
Priority to JP2011503351A priority patent/JP5653902B2/ja
Priority to AT09730490T priority patent/ATE555092T1/de
Priority to CN200980111846XA priority patent/CN101983190A/zh
Publication of WO2009124627A1 publication Critical patent/WO2009124627A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • the present invention relates to organic semiconductors and their use in organic electronic devices.
  • Organic semiconductors are being developed for a variety of electronic applications.
  • OLEDs organic electroluminescent devices
  • the structure of organic electroluminescent devices (OLEDs) in which these organic semiconductors are used as functional materials is described, for example, in US Pat. No. 4,539,507, US Pat. No. 5,151,629, EP 0676461 and WO 98/27136.
  • further improvements to the use of these devices for high quality and long lasting displays are desirable.
  • the compounds have a high thermal stability and a high glass transition temperature and can sublime undecomposed. In particular, for use at elevated temperature, a high glass transition temperature is essential for achieving high lifetimes.
  • 9,9-diphenylfluorene derivatives which are substituted on both phenyl groups in each case in the 3 'and 5' position, are very well suited for use in organic electroluminescent devices, where they lead to significant improvements over the prior art to lead.
  • This also applies if instead of the fluorene 9,10-Dihydroanthracenderivate or corresponding heterocyclic derivatives are used.
  • These compounds and their use in organic electronic devices are therefore the subject of present invention.
  • the compounds according to the invention are particularly suitable as hole transport materials, electron or exciton blocking materials, matrix materials for fluorescent or phosphorescent compounds, hole blocking materials and electron transport materials.
  • JP 2007/049055 discloses 9,9-diphenylfluorene derivatives which are substituted by at least one of the two phenyl groups having at least one substituted or unsubstituted pyrrole or benzimidazole group. Only structures are explicitly disclosed which are each substituted in the 4-position of the phenyl groups, ie para to the link to the fluorene, by amino groups. Structures which are substituted on a phenyl group having a plurality of pyrrole or benzimidazole group are not disclosed.
  • a 9,9-bis (triazinyl) fluorene which carries a phenyl group on each triazine group in each case in the 3,5-position, is disclosed as a hole-blocking material in phosphorescent electroluminescent devices.
  • the effect of this compound is attributed to the presence of the triazine groups in the molecule.
  • the presence of substituents in the 3,5-position of the triazine is not attributed importance.
  • the invention thus relates to compounds of the formula (1),
  • X is the same or different CR 1 or N at each occurrence, with a maximum of 3 groups X in each cycle; or two directly adjacent groups X stand for a unit of the following formula (7),
  • Z is the same or different CR 1 or N at each occurrence, with a maximum of two symbols Z for N in each cycle;
  • Ring atoms which may each be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R 2 , or a combination of these systems; It can have two or more adjacent radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R 2 , or a combination of these systems; It can have two or more adjacent
  • Substituents R 1 also together form a mono- or polycyclic, aliphatic or aromatic ring system
  • R 2 is identical or different at each occurrence H, D or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which also H atoms may be replaced by F; two or more adjacent substituents R 2 may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
  • n 1 or 2;
  • the compounds of the formula (1) preferably have a glass transition temperature TG of greater than 70 ° C., more preferably greater than 100 ° C., very particularly preferably greater than 110 ° C.
  • An aryl group in the sense of this invention contains 6 to 60 C atoms;
  • a heteroaryl group contains 2 to 60 C atoms and at least 1 heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • an aryl group or heteroaryl group is either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, for example naphthalene, anthracene, pyrene, quinoline, isoquinoline, etc. understood.
  • An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system in the sense of this invention contains 2 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferred selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups a short, non-aromatic moiety (preferably less than 10% of the atoms other than H), e.g. B. sp 3 -hybridized
  • C, N or O atom can be interrupted.
  • systems such as 9,9'-spirobifluorene, 9,9-diaryl fluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc. are to be understood as aromatic ring systems in the context of this invention.
  • aromatic or heteroaromatic ring system is understood as meaning systems in which a plurality of aryl or heteroaryl groups are linked together by single bonds, for example biphenyl, terphenyl or bipyridine.
  • a Cr to C 4 ⁇ r alkyl group in which also individual H atoms or CH 2 groups can be substituted by the abovementioned groups particularly preferably the radicals methyl, ethyl, n-propyl, i Propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s -pentyl, cyclopentyl, n -hexyl, cyclohexyl, n -heptyl, cycloheptyl, n-octyl, cyclooctyl , 2-ethylhexyl, trifluoromethyl, pentafluoroethyl and 2,2,2-trifluoroethyl.
  • an alkenyl group is understood as meaning in particular ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl and cyclooctenyl.
  • an alkynyl group is understood as meaning, in particular, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
  • a C 1 - to C 40 -alkoxy group is particularly preferably understood to mean methoxy, T ⁇ fluor- methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methyl butoxy.
  • aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms, which may be substituted in each case with the abovementioned radicals R and which may be linked via any position on the aromatic or heteroaromatic, are understood in particular groups which are derived from Benzene, naphthalene, anthracene, phenanthrene, benzanthracene, pyrene, chrysene, perylene, fluoranthene, naphthacene, Pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrenes, cis or trans indenofluorene, Truxen, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzo
  • Phenanthridine benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyrimididazole, pyrazine imidazole, quinoxaline imidazole, oxazole, Benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole,
  • the symbol X is the same or different at each occurrence for CR 1 or N, with at most one symbol X per cycle in the fluorene unit for N and where either all the symbols X in the substituent in the 9-position of the fluorene unit stand for CR 1 or all symbols X stand for N.
  • exactly two adjacent groups X represent a unit of the abovementioned formula (7).
  • the substituents in the 9-position of the fluorene are thus preferably 3,5-substituted phenyl or triazine. The same applies if the central unit is not a fluorene but one of the other derivatives encompassed by formula (1).
  • the symbol X stands for CR 1 .
  • the symbol Z in the unit according to formula (7) preferably stands for CR 1 .
  • a preferred embodiment of the compounds of the formula (1) are the compounds of the formulas (2), (3), (8), (9), (10) and (11)
  • n 2
  • a further preferred embodiment of the compounds of the formula (1) are the compounds of the formulas (4a) and (4b)
  • a particularly preferred embodiment of the invention are the compounds of the following formulas (4c), (4d), (8c), (8d), (9c), (9d), (10c), (10d), (11c) and (11d )
  • the symbol R in compounds of the abovementioned formula is identical or different at each occurrence for NAr 2 , C (OO) Ar, P (OO) Ar 2 or for one aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 1 .
  • R when it is bonded to a triazine group, particularly preferably stands for an aryl or heteroaryl group having 5 to 10 aromatic ring atoms.
  • R are Cl 1 Br, I and triflate, in particular Br, since these are valuable intermediates in the synthesis of further compounds according to the invention.
  • radical R or R 1 stands for a group N (Ar) 2
  • this group is preferably selected from the groups of the formula (5) or the formula (6),
  • E is a single bond, O, S, N (R 2 ) or C (R 2 ) 2 ;
  • Ar 1 is identical or different at each occurrence an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms or a triarylamine group having 15 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 2 , preferably an aryl or heteroaromatic aryl group having 6 to 14 aromatic ring atoms or one
  • Triarylamine group having 18 to 30 aromatic ring atoms, preferably having 18 to 22 aromatic ring atoms, which may be substituted in each case with one or more radicals R 2 ;
  • p is the same or different 0 or 1 at each occurrence.
  • Ar 1 is more preferably identical or different at each occurrence of phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 2-, 3- or 4-tri- phenylamine, 1- or 2-naphthyldiphenylamine, which in each case via the naphthyl or the phenyl group may be bonded, or 1- or 2-dinaphthylphenylamine, which may each be bonded via the naphthyl or the phenyl group, N-carbazolyl or N-phenyl-2-carbazolyl or N-phenyl-3-carbazolyl. These groups may each be substituted by one or more alkyl groups having 1 to 4 C atoms or by fluorine.
  • radical R or R 1 represents an aromatic or heteroaromatic ring system
  • this is preferably selected from aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, in particular having 6 to 20 aromatic ring atoms, very particularly preferably from phenyl, 1 Naphthyl, 2-naphthyl, anthracenyl, phenylanthracenyl, 1- or 2-naphthylanthracenyl, binaphthyl, pyrenyl, fluoranthenyl, 2-, 3-, A-, 5-, 6- or 7-benzanthracenyl, N -benzimidazolyl, phenyl-N benzimidazolyl, N-phenylbenzimidazolyl or phenyl-N-phenylbenzimidazolyl.
  • the symbol R 1 in compounds of the abovementioned formulas is identical or different at each occurrence for H, F, N (Ar) 2, a straight-chain alkyl group having 1 to 6 C atoms or a branched or cyclic one Alkyl group having 3 to 6 carbon atoms, each of which may be substituted by one or more radicals R 2 , wherein one or more H atoms may be replaced by F, or an aromatic or heteroaromatic ring system having 5 to 14 aromatic ring atoms, each may be substituted by one or more radicals R 2 ; Two or more adjacent substituents R 1 may also together form a mono- or polycyclic, aliphatic or aromatic ring system.
  • R 1 is the same or different each occurrence of H, F, methyl, ethyl, iso-propyl or tert-butyl, in particular H.
  • R 1 is also linear or branched alkyl chains of up to 10 C atoms are preferred.
  • -C ⁇ C- or -O- may be replaced and wherein one or more H atoms may be replaced by F, or aryl groups having 6 to 20 C atoms or heteroaryl groups having 2 to 20 C atoms, each with one or more a plurality of R 2 may be substituted, or a combination of two or three of these systems; in this case, two of the radicals R 1 , both are bound to Y, also together form a ring system and thus form a spiro system.
  • radicals R 1 which are bonded to the bridges Y, are the same or different at each occurrence and are selected from methyl, ethyl, isopropyl, tert-butyl, wherein in each case one or more H atoms may be replaced by F. or aryl groups having 6 to 14 C atoms which may be substituted by one or more R 2 radicals; two radicals R 1 can also form a ring system with each other. For compounds processed from solution, linear or branched alkyl chains of up to 10 carbon atoms are also preferred.
  • the bridge Y is a group NR 1
  • the group R 1 is also more preferably selected from an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms.
  • Examples of preferred compounds according to the formulas (1) to (4) are the structures (1) to (276) depicted below.
  • the compounds of the formula (1) according to the invention can be prepared by synthesis steps generally known to the person skilled in the art.
  • As starting compound for symmetrically substituted compounds of the invention can, for. 3,3 ', 5,5'-tetrabromobenzophenone (Eur. J. Org. Chem. 2006, 2523-2529). This can be z. B.
  • the organolithium compounds required for this reaction can be prepared by transmetalation of the corresponding aryl bromides (2-bromobiphenyl, 2-bromodiphenyl ether, 2-bromodiphenyl thioether, 2- (2-bromophenyl) -2-phenyl-1,3-dioxolane, 2-bromophenyl-diphenylamine, etc .) With alkyl lithium compounds, such as n-butyl lithium. Analogously, it is of course possible to use the corresponding Grignard compounds.
  • the tetrabromides thus produced can be further converted by methods known to those skilled in the art.
  • the palladium-catalyzed reaction with boronic acids (Suzuki coupling) or palladium-catalyzed reaction with organozinc compounds (Negishi coupling) leads to aromatic or heteroaromatic compounds according to the invention (Scheme 2).
  • the bromine function can be converted into an electrophilic group by transmetallation with organolithium compounds or Grignard compounds, which are then reacted with a plurality of electrophiles, such as.
  • organolithium compounds or Grignard compounds such as.
  • the compounds thus obtained may be end products according to the invention or intermediates, which can be further reacted ,
  • This is exemplary exemplified by the preparation of a ketone of the invention, a phosphine oxide and a benzimidazole (Scheme 4).
  • Unsymmetrically substituted compounds of this invention can be prepared by the sequence of Scheme 5 starting from fluorenone and analogous aryl ketones by addition of an aryl metal compound, e.g. 1-lithio-3,5-dibromobenzene, to the carbonyl function, conversion of the bromoaromatic compound according to one of the abovementioned methods with formation of the one functionality and subsequent introduction of the other functionality via acid-catalyzed Friedel-Crafts arylation to 1,3-diol Bromobenzene and conversion of the bromoaromatic can be obtained by one of the above methods (see, for example, Org. Lett. 2001, 3 (15), 2285.).
  • an aryl metal compound e.g. 1-lithio-3,5-dibromobenzene
  • the invention further provides a process for the preparation of the compounds of the formula (1) comprising the reaction of bis (3,5-dibromo) benzophenone with a substituted or unsubstituted 2-lithiobiphenyl, 2-lithiodiphenyl ether, 2-lithiodiphenyl thioether, 2- ( 2-lithiophenyl) -2-phenyl-1,3-dioxolane, 2-lithiophenyldiphenylamine or the corresponding Grignard compound to the triarylmethanols, followed by cyclization under acidic conditions and optionally followed by further reaction of the bromo groups.
  • the compounds according to the invention described above in particular compounds which are substituted by reactive leaving groups, such as bromine, iodine, triflate, tosylate, boronic acid or boronic esters, can be used as monomers for producing corresponding dimers, trimers, tetramers, pentamers, oligomers, polymers or as the core of dendrimers.
  • the oligomerization or polymerization is preferably carried out via the halogen functionality or the boronic acid functionality. This applies in particular to connections according to
  • Another object of the invention are therefore dimers, trimers, tetra mers, pentamers, oligomers, polymers or dendrimers containing one or more compounds of formula (1), wherein one or more radicals R 1 or R 2 bonds between the compounds of formula (1 ) in the dimer, trimer, tetramer or pentamer or bonds of the compound according to formula (1) to the polymer, oligomer or dendrimer or wherein this bond takes place via substituents on the groups R.
  • An oligomer in the context of this invention is understood as meaning a compound which has at least six units of the formula (1).
  • the polymers, oligomers or dendrimers may be conjugated, partially conjugated or non-conjugated.
  • the trimers, tetramers, pentamers, oligomers or polymers can be linear or branched.
  • the units of formula (1) may be directly linked or may be linked together via a divalent group, for example via a substituted or unsubstituted alkylene group, via a heteroatom or via a divalent aromatic or heteroaromatic group.
  • three or more units of formula (1) may be linked via a trivalent or higher valent group, for example via a trivalent or higher valent aromatic or heteroaromatic group, to a branched trimer, tetramer, pentamer, oligomer or polymer.
  • repeat units of formula (1) in dimers, trimers, tetramers, pentamers, oligomers and polymers have the same preferences as described above.
  • Preferred repeat units are therefore also here the units according to the abovementioned formulas.
  • the monomers according to the invention are homopolymerized or copolymerized with further monomers.
  • Suitable and preferred comonomers are selected from fluorenes (eg according to EP 842208 or WO 00/22026), spirobifluorenes (eg according to EP 707020, EP 894107 or WO 06/061181), paraphenylenes (eg.
  • WO 92/18552 carbazoles (eg according to WO 04/070772 or WO 04/113468), thiophenes (eg according to EP 1028136), dihydrophenanthrenes (eg according to WO 05/014689), cis and trans-indenofluorenes (for example according to WO 04/041901 or WO 04/113412), ketones (for example according to WO 05/040302), phenanthrenes (for example according to WO 05/104264 or WO 07 / 017066) or more of these units.
  • the polymers, oligomers and dendrimers usually also contain further units, for example emitting (fluorescent or phosphorescent) units, such as.
  • Vinyltriarylamines for example according to WO 07/068325
  • phosphorescent metal complexes for example according to WO 06/003000
  • charge transport units for example, if one or more groups
  • R stand for NAr 2 .
  • Another object of the present invention are mixtures containing at least one compound of formula (1) or a corresponding dimer, trimer, tetramer, pentamer, oligomer or polymer and at least one further compound.
  • the further compound may be, for example, a fluorescent or phosphorescent dopant, if the compound of formula (1) is used as matrix material. Suitable fluorescent and phosphorescent dopants are listed below in connection with the organic electroluminescent devices and are also preferred for the mixtures according to the invention.
  • the further compound may also be a dopant if the compound according to formula (1) is a hole transport or electron transport compound. Suitable dopants are listed below in connection with the organic electroluminescent devices.
  • Solutions containing at least one compound of the formula (1) or a corresponding dimer, trimer, tetramer, pentamer, oligomer or polymer and at least one organic solvent are required for the preparation of the organic electronic device from solution, for example by spin coating or by printing processes.
  • the compounds according to the invention of formula (1) and corresponding dimers, trimers, tetramers, pentamers, oligomers, polymers or dendrimers are suitable for use in electronic devices, in particular in organic electroluminescent devices (OLEDs, PLEDs). Depending on the substitution, the compounds are used in different functions and layers.
  • OLEDs organic electroluminescent devices
  • PLEDs organic electroluminescent devices
  • the preferred embodiments correspond to the abovementioned formulas.
  • Another object of the invention is therefore the use of compounds according to formula (1) or corresponding dimers, trimers, tetramers, pentamers, oligomers, polymers or dendrimers in electronic devices, in particular in organic electroluminescent devices.
  • organic electronic devices comprising at least one compound according to formula (1) or a corresponding dimer, trimer, tetramer,
  • Pentamer, oligomer, polymer or dendrimer in particular organic electroluminescent devices containing anode, cathode and at least one emitting layer, characterized in that at least one organic layer, which may be an emitting layer or another layer, at least one compound according to
  • the organic electroluminescent device may contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, charge generation layers (IDMC 2003, Taiwan, Session 21 OLED (5), T. Matsumoto, T. Nakada).
  • the layers in particular the charge transport layers, may also be doped.
  • the doping of the layers may be advantageous for improved charge transport. It should be noted, however, that not necessarily each of these layers must be present and the choice of the layers always depends on the compounds used and in particular also on the fact whether it is a fluorescent or phosphorescent electroluminescent device.
  • the organic electroluminescent device contains a plurality of emitting layers, wherein at least one organic layer contains at least one compound according to formula (1).
  • Emission layers have a total of several emission maxima between 380 nm and 750 nm, so that a total of white emission results, ie in the emitting layers different emitting compounds are used, which can fluoresce or phosphoresce and emit the blue and yellow, orange or red light.
  • Particularly preferred are three-layer systems, ie systems with three emitting layers, wherein at least one of these layers at least one compound according to formula (1) contains and wherein the three layers blue, green and orange or red emission show (for the basic structure see, for. WO 05/011013).
  • white emission emitters which have broadband emission bands and thereby show white emission.
  • the compounds of the formula (1) are used as matrix material for fluorescent or phosphorescent compounds in an emitting layer.
  • the same preferences apply to the groups R and R 1 in structures of the formula (2), (3) and (4).
  • Compounds are preferably one or more groups R and / or R 1 for an aromatic or heteroaromatic ring system, in particular for an aromatic ring system containing anthracene.
  • the same preferences apply to the groups R and R 1 in structures according to the abovementioned formulas.
  • a matrix material is understood in a system of matrix and dopant that component which is present in the system in the higher proportion.
  • the matrix is understood to be the component whose proportion is the highest in the mixture.
  • a mixture is used as matrix, wherein at least one component of this mixture is a compound of formula (1).
  • Preferred is a Component of this mixture a hole transport compound and the other an electron transport compound.
  • Preferred hole transport compounds are aromatic amines and carbazole derivatives.
  • Preferred electron transport compounds are aromatic ketones.
  • the compound of the formula (1) When used as a matrix material for an emitting compound in an emitting layer, it may be used in combination with one or more phosphorescent materials (triplet emitters).
  • phosphorescence is understood as meaning the luminescence from an excited state with a higher spin multiplicity, ie a spin state> 1, in particular from an excited triplet state.
  • all in particular luminescent iridium, platinum, osmium, gold and copper compounds are referred to as phosphorescent materials.
  • the mixture of the compound according to formula (1) and the emitting compound then contains between 99 and 1
  • Wt .-% preferably between 98 and 10 wt .-%, particularly preferably between 97 and 60 wt .-%, in particular between 95 and 85 wt .-% of the compound according to formula (1) based on the total mixture of emitter and matrix material .
  • the mixture contains between 1 and 99 wt .-%, preferably between 2 and 90 wt .-%, more preferably between 3 and 40 wt .-%, in particular between 5 and 15 wt .-% of the emitter based on the total mixture of Emitter and matrix material.
  • Suitable phosphorescent compounds are, in particular, compounds which emit light, preferably in the visible range, with suitable excitation and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80.
  • Preferred phosphorescence emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium or platinum.
  • emitters described above can be found in the applications WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614 and WO 05/033244.
  • suitable emitters are the abovementioned compounds according to the invention.
  • OLEDs are used and as they are known in the art of organic electroluminescence, and the skilled artisan can use other phosphorescent complexes without inventive step.
  • the proportion of the matrix material in the emitting layer is between 50.0 and 99.9% by weight, preferably between 80.0 and 99.5% by weight, particularly preferably between 90.0 and 99.0 wt .-%. Accordingly, the proportion of the dopant is between 0.1 and 50.0 wt .-%, preferably between 0.1 and 20.0 wt .-%, more preferably between 0.5 and 15 wt .-%, most preferably between 1.0 and 10.0 wt .-%.
  • Preferred dopants are selected from the class of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers and arylamines.
  • a monostyrylamine is understood as meaning a compound which contains a substituted or unsubstituted styryl group and at least one, preferably aromatic, amine.
  • a distyrylamine is understood as meaning a compound which contains two substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • a tristyrylamine is understood as meaning a compound which contains three substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • a tetrastyrylamine is meant a compound containing four substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
  • the styryl groups are particularly preferred stilbenes, which may also be further substituted.
  • Corresponding phosphines and ethers are defined in analogy to the amines. Under an aryl amine or an aromatic amine in the sense This invention is a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen.
  • At least one of these aromatic or heteroaromatic ring systems is preferably a fused ring system, preferably having at least 14 aromatic ring atoms.
  • Preferred examples thereof are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
  • aromatic anthracene amine is meant a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • An aromatic anthracenediamine is understood as meaning a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position.
  • Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, the diarylamino groups being preferably attached to the pyrene in the 1-position or in the 1,6-position.
  • Further preferred dopants are selected from indenofluorenamines or diamines, for example according to WO 06/122630, benzoindenofluorenamines or diamines, for example according to WO 08/006449, and dibenzoindenofluorenamines or diamines, for example according to WO 07/140847.
  • dopants from the class of styrylamines are substituted or unsubstituted tristilbene amines or the dopants described in WO 06/000388, WO 06/058737, WO 06/000389, WO 07/065549 and WO 07/115610.
  • Compounds according to formula (1) are used as hole transport material or as hole injection material or as electron blocking material or as exciton blocking material.
  • the compounds are then preferably substituted with at least one group N (Ar) 2, preferably with at least two groups N (Ar) 2 and / or they contain further groups which contain the
  • the groups R for N (Ar) 2 are preferably selected from the above-described formulas (5) or (6). This applies in particular to the radicals R on the structures according to the abovementioned formulas.
  • Other preferred groups that improve hole transport are, for example, the Groups N (R 1 ), S or O, in particular N (R 1 ) as bridge Y or electron-rich heteroaromatics, in particular thiophene, pyrrole or furan as group R or R 1 .
  • the compound is preferably used in a hole transport or in a hole injection or in an electron blocking or in an exciton blocking layer.
  • a hole injection layer in the sense of this invention is a layer that is directly adjacent to the anode.
  • a hole transport layer in the sense of this invention is a layer that lies between a hole injection layer and an emission layer.
  • An electron blocking or exciton blocking layer in the sense of this invention is a layer which directly adjoins an emitting layer on the anode side.
  • the compounds according to formula (1) are used as electron transport material or as hole blocking material in an electron transport layer or a hole blocking layer.
  • a hole blocking layer in the sense of this invention is a layer which lies on between an emitting layer and an electron transport layer and directly adjoins the emitting layer.
  • the compound of the formula (1) When the compound of the formula (1) is used as the electron transport material, it may be preferable to use it as a mixture with another compound.
  • Preferred mixture components are alkali metal compounds, preferably lithium compounds, particularly preferably Liq (lithium quinolinate) or Liq derivatives.
  • repeating units of the formula (1) can also be used either as a polymer backbone, as a hole-transporting unit and / or as an electron-transporting unit.
  • the preferred substitution patterns correspond to those described above.
  • an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process.
  • the materials are vapor-deposited in vacuum sublimation systems at a pressure of less than 10 '5 mbar, preferably less than 10 ' 6 mbar. It should be noted, however, that the pressure can be even lower, for example less than 10 -7 mbar.
  • an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
  • the materials are applied at a pressure between 10 "applied 5 mbar and 1 bar.
  • OVJP organic vapor jet printing
  • the materials are applied directly through a nozzle and patterned (eg. BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
  • an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
  • any printing process such as screen printing, flexographic printing or offset printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (ink jet printing), are produced.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • inkjet printing ink jet printing
  • soluble compounds are needed. High solubility can be achieved by suitable substitution of the compounds.
  • the compounds of the invention have a high thermal stability and can sublime undecomposed.
  • Single bond or S, O or N (R 1 ) included as group Y and / or which are substituted with electron-rich heteroaromatics, are very suitable for use as hole injection and hole transport material and lead to a reduction of the operating voltage.
  • the OLEDs prepared with the compounds according to the invention generally have a very long service life.
  • the OLEDs prepared with the compounds according to the invention generally have a very high quantum efficiency.
  • organic field-effect transistors O-FETs
  • organic thin-film transistors O-TFTs
  • organic light-emitting transistors O-LETs
  • organic integrated circuits O-ICs
  • organic solar cells O-SCs
  • organic field quench devices O-FQDs
  • LECs organic laser diodes
  • O-lasers organic photoreceptors.
  • the solvents and reagents can be obtained from ALDRICH or ABCR.
  • the precursor 3,3 ', 5,5'-tetrabromobenzophenone is prepared according to Eur. J. Org. Chem. 2006, 2523-2529.
  • the corresponding Grignard compound is prepared in a mixture of 500 ml of tetrahydrofuran and 250 ml of dimethoxyethane. Then at room temperature with a suspension of 224.0 g (450 mmol) of bis (3,5-dibromophenyl) ketone in 1000 ml of tetrahydrofuran added and stirred for twelve hours. The solvent is removed in vacuo, the residue is treated with 1000 ml of glacial acetic acid and 5 ml of hydrogen bromide and stirred for one hour.
  • Example 4 Analogously to Example 4, the following compounds according to the invention are obtained from the corresponding boronic acids (Examples 5-7):
  • Example 8 Analogously to Example 8, the following compounds according to the invention are obtained from the corresponding amines and the corresponding fluorenes (Examples 9-13):
  • a suspension of 50.7 g (80 mmol) of 9,9-bis (3,5-dibromophenyl) fluorene, 78.6 g (470 mmol) of carbazole and 201.7 g (950 mmol) of tripotassium phosphate is mixed with 500 g of glass beads in 1000 ml of p-xylene well stirred.
  • the suspension is treated with 1.62 g (8.0 mmol) of tri-ferf-butylphosphine and 894 mg (4.0 mmol) of palladium (II) acetate and refluxed for five days. After cooling, it is mixed with 1000 ml of water, stirred for twelve hours and then filtered.
  • Example 14 Analogously to Example 14, the following compounds according to the invention are obtained from the corresponding carbazole derivatives (Examples 15-16):
  • Example 17 Analogously to Example 17, the following compounds according to the invention are obtained from the corresponding nitriles (Examples 18 and 19):
  • Example 21 Analogously to Example 20, the following compound according to the invention is obtained from the corresponding chlorophosphine (Example 21):
  • a solution of 16.6 g (100 mmol) of fluorene in 500 ml of THF is mixed with 7.2 g (300 mmol) of sodium hydride. After addition of 0.5 ml of diisopropylamine, the mixture is stirred for 1 h at room temperature, then treated dropwise with a solution of 58.9 g (220 mmol) of 2-chloro-4,6-diphenyl-1, 3,5-triazine and then 16 Stirred at 50 0 C h. After cooling, the mixture is quenched by addition of 5 ml of water, the THF is stripped off in vacuo, the residue is dissolved in dichloromethane, the organic phase is washed with water and then dried over magnesium sulfate.
  • N-phenylcarbazole in 500 ml of THF is added dropwise with 24.0 ml (60 mmol) of n-butyllithium (2.5 N in hexane), followed by 30 min. stirred at -78 0 C and then added dropwise with a solution of 38.0 g (60 mmol) of 9,9-bis (3,5-dibromophenyl) fluorene in 100 ml of THF.
  • Electroluminescent devices according to the invention can be prepared as described, for example, in WO 05/003253. Here the results of different OLEDs are compared.
  • the basic structure, the materials used, the degree of doping and their layer thicknesses are identical for better comparability.
  • the first example describes a comparative standard Device according to the ⁇ 5 prior art in which the emission layer of the host material Bis (9,9'-spirobifluoren-2-yl) ketone and the guest material (dopant) lr (ppy) 3 .
  • OLEDs of various constructions are described, in each case the guest material (dopant) is lr (ppy) 3 .
  • OLEDs are produced with the following structure:
  • HIL Hole Injection Layer 20 nm 2,2 ', 7,7'-tetrakis (di-para-tolylamino) spiro-9,9'-bifluorene
  • HTL Hole transport layer
  • NPB N-naphthyl-N-phenyl-4,4 1 -diaminobiphenyl
  • Emission layer EML 40 nm
  • Host spiro-ketone (SK) (bis (bis) 9,9 ' - spirobifluoren-2-yl) ketone) as a comparison or compound 2.
  • Dotand Ir (ppy) 3 (10% doping, evaporated, synthesized according to WO 04/085449).
  • amine-1 is a comparative compound according to the closest prior art (JP 2005/085599):
  • OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) as a function of the brightness, calculated from current-voltage-brightness characteristics (ILJL characteristics), and the lifetime are determined.
  • the lifetime at an initial luminance of 1000 cd / m 2 is comparable to Comparative Example 26 at 7400 h (see Table 1, Example 28).
  • the lifetime at an initial luminance of 1000 cd / m 2 is comparable to 6900 h as when using the spiro-ketone (see Table 1, Example 29).
  • Compound 6 is useful inter alia as an electron conductor that provides good efficiencies and lifetimes at low voltages.

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Abstract

La présente invention concerne des dérivés du fluor et des dispositifs électroniques organiques dans lesquels on utilise ces composés sous forme de matrice dans la couche émettrice et/ou sous forme de matériau de transport de trous et/ou de matière bloquant les électrons ou les excitons et/ou sous forme de matériau de transport d'électrons.
PCT/EP2009/001736 2008-04-07 2009-03-11 Dérivés du fluor pour dispositifs électroluminescents organiques Ceased WO2009124627A1 (fr)

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EP09730490A EP2260023B1 (fr) 2008-04-07 2009-03-11 Dérivés du fluorène pour dispositifs électroluminescents organiques
US12/936,644 US8361638B2 (en) 2008-04-07 2009-03-11 Fluorine derivatives for organic electroluminescence devices
JP2011503351A JP5653902B2 (ja) 2008-04-07 2009-03-11 有機エレクトロルミネセント素子用フッ素誘導体
AT09730490T ATE555092T1 (de) 2008-04-07 2009-03-11 Fluorenderivate für organische elektrolumineszenzvorrichtungen
CN200980111846XA CN101983190A (zh) 2008-04-07 2009-03-11 用于有机电致发光器件的氟衍生物

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Cited By (101)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010137601A1 (fr) 2009-05-29 2010-12-02 Semiconductor Energy Laboratory Co., Ltd. Dérivé de fluorène, élément émetteur de lumière, dispositif émetteur de lumière, dispositif électronique et dispositif d'éclairage
WO2011032626A1 (fr) 2009-09-16 2011-03-24 Merck Patent Gmbh Complexes métalliques
EP2301926A1 (fr) 2008-06-05 2011-03-30 Idemitsu Kosan Co., Ltd. Composé halogéné, composé polycyclique, et élément électroluminescent organique comprenant le composé polycyclique
DE102009053644A1 (de) 2009-11-17 2011-05-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
WO2011060877A2 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
DE102010004803A1 (de) 2010-01-16 2011-07-21 Merck Patent GmbH, 64293 Materialien für organische Elektrolumineszenzvorrichtungen
WO2011126063A1 (fr) * 2010-04-05 2011-10-13 住友化学株式会社 Composites de métal et composé utile pour leur préparation
WO2011137922A1 (fr) 2010-05-03 2011-11-10 Merck Patent Gmbh Formulations et dispositifs électroniques
DE102010024897A1 (de) 2010-06-24 2011-12-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US20120018717A1 (en) * 2009-03-30 2012-01-26 Duksan High Metal Co., Ltd. Organic electronic device, compounds for same, and terminal
WO2012014500A1 (fr) * 2010-07-30 2012-02-02 保土谷化学工業株式会社 Composé ayant une structure de noyau indénocarbazole et élément électroluminescent organique
DE102010045405A1 (de) 2010-09-15 2012-03-15 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
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WO2012089294A1 (fr) * 2010-12-28 2012-07-05 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2012074210A3 (fr) * 2010-12-02 2012-07-26 제일모직 주식회사 Composé pour un dispositif opto-électronique organique, élément émetteur de lumière organique le comprenant, et dispositif d'affichage comprenant l'élément émetteur de lumière organique
WO2012110178A1 (fr) 2011-02-14 2012-08-23 Merck Patent Gmbh Dispositif et procédé de traitement de cellules et de tissu cellulaire
WO2012126566A1 (fr) 2011-03-24 2012-09-27 Merck Patent Gmbh Matériaux fonctionnels ioniques organiques
WO2012136296A1 (fr) 2011-04-04 2012-10-11 Merck Patent Gmbh Complexes métalliques
WO2012152366A1 (fr) 2011-05-12 2012-11-15 Merck Patent Gmbh Composés ioniques organiques, compositions et dispositifs électroniques
JP2012531737A (ja) * 2009-06-25 2012-12-10 チェイル インダストリーズ インコーポレイテッド 有機光電子素子用化合物、それを含む有機発光ダイオード、および前記有機発光ダイオードを含む表示装置
WO2013100467A1 (fr) * 2011-12-30 2013-07-04 제일모직 주식회사 Composé pour dispositif optoélectronique organique, diode organique émettant de la lumière le comprenant et dispositif d'affichage comprenant une diode organique émettant de la lumière
WO2013100464A1 (fr) * 2011-12-29 2013-07-04 제일모직 주식회사 Composé pour un élément optoélectronique organique, élément organique émettant de la lumière le comprenant et dispositif d'affichage comprenant l'élément organique émettant de la lumière
WO2013107487A1 (fr) 2012-01-16 2013-07-25 Merck Patent Gmbh Complexes organométalliques
WO2013113349A1 (fr) 2012-01-30 2013-08-08 Merck Patent Gmbh Nanocristaux sur fibres
WO2013120577A1 (fr) 2012-02-14 2013-08-22 Merck Patent Gmbh Composés de spirobifluorène pour dispositifs organiques électroluminescents
KR20140009184A (ko) * 2010-10-14 2014-01-22 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
TWI425076B (zh) * 2011-11-01 2014-02-01 Ind Tech Res Inst 咔唑衍生物及包含此衍生物之有機發光二極體
WO2014023388A1 (fr) 2012-08-10 2014-02-13 Merck Patent Gmbh Matériaux pour dispositifs organiques à électroluminescence
WO2014079532A1 (fr) 2012-11-20 2014-05-30 Merck Patent Gmbh Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques
US8927118B2 (en) 2008-06-05 2015-01-06 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
WO2015135625A1 (fr) 2014-03-13 2015-09-17 Merck Patent Gmbh Formulations de composés luminescents
WO2015197156A1 (fr) 2014-06-25 2015-12-30 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016184540A1 (fr) 2015-05-18 2016-11-24 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2017012687A1 (fr) 2015-07-22 2017-01-26 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2017194435A1 (fr) 2016-05-11 2017-11-16 Merck Patent Gmbh Compositions pour cellules électrochimiques
WO2017207596A1 (fr) 2016-06-03 2017-12-07 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018104194A1 (fr) 2016-12-05 2018-06-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018104193A1 (fr) 2016-12-05 2018-06-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018127465A1 (fr) 2017-01-04 2018-07-12 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018138306A1 (fr) 2017-01-30 2018-08-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018149769A1 (fr) 2017-02-14 2018-08-23 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2019081391A1 (fr) 2017-10-24 2019-05-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2019145316A1 (fr) 2018-01-25 2019-08-01 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2019233904A1 (fr) 2018-06-07 2019-12-12 Merck Patent Gmbh Dispositifs electroluminescents organiques
WO2020011686A1 (fr) 2018-07-09 2020-01-16 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2020094542A1 (fr) 2018-11-06 2020-05-14 Merck Patent Gmbh Dérivés de 5,6-diphényl-5,6-dihydro-dibenzo[c,e][1,2]azaphosphorine et de 6-phényl-6h-dibenzo[c,e][1,2]thiazine-5,5-dioxyde et composés similaires en tant que matériaux organiques d'électroluminescence pour des oled
WO2020099307A1 (fr) 2018-11-15 2020-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2020127165A1 (fr) 2018-12-19 2020-06-25 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2020148303A1 (fr) 2019-01-17 2020-07-23 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2021043755A1 (fr) 2019-09-03 2021-03-11 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2021078831A1 (fr) 2019-10-25 2021-04-29 Merck Patent Gmbh Composés pouvant être utilisés dans un dispositif électronique organique
WO2021122538A1 (fr) 2019-12-18 2021-06-24 Merck Patent Gmbh Composés aromatiques pour dispositifs électroluminescents organiques
WO2021122740A1 (fr) 2019-12-19 2021-06-24 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
WO2021151922A1 (fr) 2020-01-29 2021-08-05 Merck Patent Gmbh Dérivés de benzimidazole
WO2021170522A1 (fr) 2020-02-25 2021-09-02 Merck Patent Gmbh Utilisation de composés hétérocycliques dans un dispositif électronique organique
WO2021175706A1 (fr) 2020-03-02 2021-09-10 Merck Patent Gmbh Utilisation de composés sulfone dans un dispositif électronique organique
WO2021185712A1 (fr) 2020-03-17 2021-09-23 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques
WO2021185829A1 (fr) 2020-03-17 2021-09-23 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2021191183A1 (fr) 2020-03-26 2021-09-30 Merck Patent Gmbh Composés cycliques pour dispositifs électroluminescents organiques
WO2021204646A1 (fr) 2020-04-06 2021-10-14 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
WO2022002771A1 (fr) 2020-06-29 2022-01-06 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022002772A1 (fr) 2020-06-29 2022-01-06 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques
WO2022069422A1 (fr) 2020-09-30 2022-04-07 Merck Patent Gmbh Composés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques
WO2022069421A1 (fr) 2020-09-30 2022-04-07 Merck Patent Gmbh Composés pouvant être utilisés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques
WO2022079068A1 (fr) 2020-10-16 2022-04-21 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022079067A1 (fr) 2020-10-16 2022-04-21 Merck Patent Gmbh Composés comprenant des hétéroatomes pour dispositifs électroluminescents organiques
WO2022101171A1 (fr) 2020-11-10 2022-05-19 Merck Patent Gmbh Composés sulfureux pour dispositifs électroluminescents organiques
WO2022117473A1 (fr) 2020-12-02 2022-06-09 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022129114A1 (fr) 2020-12-18 2022-06-23 Merck Patent Gmbh Composés azotés pour dispositifs électroluminescents organiques
WO2022129116A1 (fr) 2020-12-18 2022-06-23 Merck Patent Gmbh Dérivés d'indolo[3.2.1-jk]carbazole-6-carbonitrile utilisés en tant qu'émetteurs fluorescents bleus destinés à être utilisés dans des oled
WO2022129113A1 (fr) 2020-12-18 2022-06-23 Merck Patent Gmbh Composés hétéroaromatiques azotés pour dispositifs électroluminescents organiques
WO2022157343A1 (fr) 2021-01-25 2022-07-28 Merck Patent Gmbh Composés azotés pour dispositifs électroluminescents organiques
WO2022184601A1 (fr) 2021-03-02 2022-09-09 Merck Patent Gmbh Composés pour dispositifs électroluminescents organiques
WO2022194799A1 (fr) 2021-03-18 2022-09-22 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques
WO2022229234A1 (fr) 2021-04-30 2022-11-03 Merck Patent Gmbh Composés hétérocycliques azotés pour dispositifs électroluminescents organiques
WO2023041454A1 (fr) 2021-09-14 2023-03-23 Merck Patent Gmbh Composés hétérocycliques contenant du bore pour dispositifs électroluminescents organiques
WO2023072799A1 (fr) 2021-10-27 2023-05-04 Merck Patent Gmbh Composés hétérocycliques contenant du bore et de l'azote pour dispositifs électroluminescents organiques
WO2023117835A1 (fr) 2021-12-21 2023-06-29 Merck Patent Gmbh Dispositifs électroniques
WO2023117836A1 (fr) 2021-12-21 2023-06-29 Merck Patent Gmbh Dispositifs électroniques
EP4236652A2 (fr) 2015-07-29 2023-08-30 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
WO2023161168A1 (fr) 2022-02-23 2023-08-31 Merck Patent Gmbh Hétérocycles aromatiques pour dispositifs électroluminescents organiques
WO2023161167A1 (fr) 2022-02-23 2023-08-31 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2023208899A1 (fr) 2022-04-28 2023-11-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2023213837A1 (fr) 2022-05-06 2023-11-09 Merck Patent Gmbh Composés cycliques pour dispositifs électroluminescents organiques
WO2023247338A1 (fr) 2022-06-20 2023-12-28 Merck Patent Gmbh Hétérocycles organiques pour dispositifs photoélectriques
WO2023247345A1 (fr) 2022-06-20 2023-12-28 Merck Patent Gmbh Hétérocycles pour dispositifs photoélectriques
WO2024061948A1 (fr) 2022-09-22 2024-03-28 Merck Patent Gmbh Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques
WO2024061942A1 (fr) 2022-09-22 2024-03-28 Merck Patent Gmbh Composés contenant de l'azote pour dispositifs électroluminescents organiques
WO2024094592A2 (fr) 2022-11-01 2024-05-10 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2024149694A1 (fr) 2023-01-10 2024-07-18 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2024153568A1 (fr) 2023-01-17 2024-07-25 Merck Patent Gmbh Hétérocycles pour dispositifs électroluminescents organiques
WO2024184050A1 (fr) 2023-03-07 2024-09-12 Merck Patent Gmbh Composés azotés cycliques pour dispositifs électroluminescents organiques
EP4486099A1 (fr) 2023-06-30 2025-01-01 Merck Patent GmbH Composés pour dispositifs électroluminescents organiques
WO2025003084A1 (fr) 2023-06-28 2025-01-02 Merck Patent Gmbh Composés dicyanoaryle pour dispositifs électroluminescents organiques
WO2025045935A1 (fr) 2023-08-31 2025-03-06 Merck Patent Gmbh Composés aromatiques contenant des groupes cyano pour dispositifs électroluminescents organiques
WO2025109056A1 (fr) 2023-11-24 2025-05-30 Merck Patent Gmbh Hétérocycles contenant de l'oxygène pour dispositifs électroluminescents organiques
WO2025132194A1 (fr) 2023-12-20 2025-06-26 Merck Patent Gmbh Nouveaux matériaux pour dispositifs électroluminescents organiques
WO2025181044A1 (fr) 2024-02-29 2025-09-04 Merck Patent Gmbh Composés contenant de l'azote pour dispositifs électroluminescents organiques
WO2025181097A1 (fr) 2024-02-29 2025-09-04 Merck Patent Gmbh Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques
WO2025181124A1 (fr) 2024-03-01 2025-09-04 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2026008276A1 (fr) 2024-07-04 2026-01-08 Merck Patent Gmbh Matériaux pour diodes électroluminescentes organiques

Families Citing this family (113)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008027005A1 (de) 2008-06-05 2009-12-10 Merck Patent Gmbh Organische elektronische Vorrichtung enthaltend Metallkomplexe
DE102008033563A1 (de) 2008-07-17 2010-01-21 Merck Patent Gmbh Komplexe mit kleinen Singulett-Triplett-Energie-Abständen zur Verwendung in opto-elektronischen Bauteilen (Singulett-Harvesting-Effekt)
DE102008033943A1 (de) * 2008-07-18 2010-01-21 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102008036247A1 (de) 2008-08-04 2010-02-11 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend Metallkomplexe
DE102008036982A1 (de) 2008-08-08 2010-02-11 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102008050841B4 (de) 2008-10-08 2019-08-01 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102009005288A1 (de) * 2009-01-20 2010-07-22 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
JP5400448B2 (ja) * 2009-03-31 2014-01-29 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子
DE102009023154A1 (de) 2009-05-29 2011-06-16 Merck Patent Gmbh Zusammensetzung, enthaltend mindestens eine Emitterverbindung und mindestens ein Polymer mit konjugationsunterbrechenden Einheiten
WO2011017341A2 (fr) * 2009-08-03 2011-02-10 The Johns Hopkins University Copolymères contenant un oligo-p-phénylène de type échelle présentant des tensions en circuit ouvert élevées et une activité photovoltaïque ambiante
EP2462203B1 (fr) 2009-08-04 2016-03-02 Merck Patent GmbH Dispositifs électroniques comprenant des hydrocarbures polycycliques
JP5784608B2 (ja) 2009-09-16 2015-09-24 メルク パテント ゲーエムベーハー 電子素子製造のための調合物
JP5897472B2 (ja) 2009-12-22 2016-03-30 メルク パテント ゲーエムベーハー エレクトロルミネセンス機能性界面活性剤
EP2517278B1 (fr) 2009-12-22 2019-07-17 Merck Patent GmbH Formulations électroluminescentes
WO2011076323A1 (fr) 2009-12-22 2011-06-30 Merck Patent Gmbh Formulations comprenant des matériaux fonctionnels à phases séparées
DE102010009193B4 (de) 2010-02-24 2022-05-19 MERCK Patent Gesellschaft mit beschränkter Haftung Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend
US9373807B2 (en) 2010-03-11 2016-06-21 Merck Patent Gmbh Radiative fibers
WO2011110277A1 (fr) 2010-03-11 2011-09-15 Merck Patent Gmbh Fibres en thérapie et cosmétique
DE102010020567A1 (de) 2010-05-14 2011-11-17 Merck Patent Gmbh Metallkomplexe
EP2576723B1 (fr) 2010-05-27 2017-09-20 Merck Patent GmbH Composition comprenant des points quantiques
DE102010027218A1 (de) 2010-07-15 2012-01-19 Merck Patent Gmbh Organische Komplexe enthaltend Metalle
JP2013539584A (ja) 2010-07-26 2013-10-24 メルク パテント ゲーエムベーハー 量子ドットおよびホスト
US20130226268A1 (en) 2010-07-26 2013-08-29 Merck Patent Gmbh Nanocrystals in devices
DE102010046412B4 (de) 2010-09-23 2022-01-13 Merck Patent Gmbh Metall-Ligand Koordinationsverbindungen
DE102010046512A1 (de) 2010-09-24 2012-03-29 Merck Patent Gmbh Phosphorhaltige Metallkomplexe
DE102010054525A1 (de) 2010-12-15 2012-04-26 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010055902A1 (de) 2010-12-23 2012-06-28 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010055901A1 (de) 2010-12-23 2012-06-28 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
UA114403C2 (uk) 2011-05-25 2017-06-12 Емерікен Дай Сорс, Інк. Похідні труксену, які містять оксим-складноефірні та/або ацильні групи
DE102011102586A1 (de) 2011-05-27 2012-11-29 Merck Patent Gmbh Organische elektronische Vorrichtung
KR20130015400A (ko) * 2011-08-03 2013-02-14 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2013045411A1 (fr) * 2011-09-28 2013-04-04 Solvay Sa Composés de spirobifluorène pour dispositifs électroluminescents
KR101981349B1 (ko) * 2011-09-28 2019-05-22 스미또모 가가꾸 가부시키가이샤 발광 소자용 스피로바이플루오렌 화합물
DE102011117422A1 (de) 2011-10-28 2013-05-02 Merck Patent Gmbh Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen
KR101954980B1 (ko) * 2011-11-03 2019-05-31 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2013097920A1 (fr) 2011-12-27 2013-07-04 Merck Patent Gmbh Complexes métalliques comprenant des 1,2,3-triazoles
JP6020472B2 (ja) * 2012-01-10 2016-11-02 コニカミノルタ株式会社 透明電極、透明電極の製造方法、電子デバイス及び有機エレクトロルミネッセンス素子
KR102198635B1 (ko) 2012-04-20 2021-01-05 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
US20130328018A1 (en) * 2012-06-12 2013-12-12 Academia Sinica Fluorine-modification process and applications thereof
KR101401639B1 (ko) 2012-07-27 2014-06-02 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR101537005B1 (ko) 2012-09-28 2015-07-20 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
CN103420785A (zh) * 2012-12-05 2013-12-04 烟台九目化学制品有限公司 一种9，9′-二(4-卤苯基)芴类衍生物的制备方法
EP2947079B1 (fr) 2013-02-07 2017-05-03 LG Chem, Ltd. Composé hétérocyclique et élément électroluminescent organique l'utilisant
CN111718281A (zh) * 2013-03-22 2020-09-29 默克专利有限公司 用于制备有机电致发光器件用材料的合成结构单元
KR102116494B1 (ko) * 2013-04-25 2020-05-29 삼성디스플레이 주식회사 유기 발광 소자
WO2014194971A1 (fr) * 2013-06-06 2014-12-11 Merck Patent Gmbh Dispositif électroluminescent organique
EP3028318A1 (fr) 2013-07-29 2016-06-08 Merck Patent GmbH Dispositif électro-optique et son utilisation
JP6588688B2 (ja) * 2014-03-27 2019-10-09 旭有機材株式会社 化合物、組成物及び硬化物
KR102251735B1 (ko) * 2014-04-14 2021-05-13 삼성디스플레이 주식회사 유기 발광 장치용 재료, 유기 발광 장치, 및 이를 포함하는 표시 장치
KR102030354B1 (ko) * 2014-05-13 2019-10-10 에스에프씨주식회사 방향족 아민기를 포함하는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
DE102014008722B4 (de) 2014-06-18 2024-08-22 Merck Patent Gmbh Zusammensetzungen für elektronische Vorrichtungen, Formulierung diese enthaltend, Verwendung der Zusammensetzung, Verwendung der Formulierung sowie organische elektronische Vorrichtung enthaltend die Zusammensetzung
EP3189551B1 (fr) 2014-09-05 2021-01-27 Merck Patent GmbH Formulations et procédé de fabrication d'un dispositif électroluminescent organique
EP3204463B1 (fr) 2014-10-08 2019-04-17 cynora GmbH Complexes métalliques présentant des ligands tridentates pour des utilisations optoélectroniques
WO2016107663A1 (fr) 2014-12-30 2016-07-07 Merck Patent Gmbh Formulations et dispositifs électroniques
US10329483B2 (en) 2014-12-30 2019-06-25 Dow Global Technologies Llc Fluorene derivatives as light emitting elements for electroluminescent devices
WO2016155866A1 (fr) 2015-03-30 2016-10-06 Merck Patent Gmbh Formulation de materiau fonctionnel organique comprenant un solvant siloxane
JP6692126B2 (ja) 2015-06-03 2020-05-13 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
KR102654992B1 (ko) 2015-06-12 2024-04-04 메르크 파텐트 게엠베하 Oled 제제에 대한 용매로서 비-방향족 사이클을 함유하는 에스테르
EP3341981B1 (fr) 2015-08-28 2020-08-19 Merck Patent GmbH Formulation d'un matériau fonctionnel organique comprenant un solvant contenant un groupe époxy
CN108368361A (zh) 2015-12-10 2018-08-03 默克专利有限公司 含有包含非芳族环的酮的制剂
JP7051684B2 (ja) 2015-12-15 2022-04-11 メルク パテント ゲーエムベーハー 有機電子調合物のための溶媒として芳香族基を含むエステル
KR20180095028A (ko) 2015-12-16 2018-08-24 메르크 파텐트 게엠베하 둘 이상의 상이한 용매의 혼합물을 함유하는 제형
EP3390549B1 (fr) 2015-12-16 2022-06-29 Merck Patent GmbH Formulations contenant un solvant solide
KR102595922B1 (ko) 2015-12-22 2023-10-31 삼성디스플레이 주식회사 카바졸계 화합물 및 이를 포함한 유기 발광 소자
US10840448B2 (en) 2016-02-17 2020-11-17 Merck Patent Gmbh Formulation of an organic functional material
GB2547645A (en) * 2016-02-22 2017-08-30 Cambridge Display Tech Ltd Compound,composition and organic light-emitting device
DE102016003104A1 (de) 2016-03-15 2017-09-21 Merck Patent Gmbh Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter
KR101850243B1 (ko) * 2016-03-28 2018-04-23 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
CN109153871A (zh) 2016-06-16 2019-01-04 默克专利有限公司 有机功能材料的制剂
JP2019523998A (ja) 2016-06-17 2019-08-29 メルク パテント ゲーエムベーハー 有機機能材料の調合物
TW201815998A (zh) 2016-06-28 2018-05-01 德商麥克專利有限公司 有機功能材料之調配物
WO2018024719A1 (fr) 2016-08-04 2018-02-08 Merck Patent Gmbh Formulation d'une matière fonctionnelle organique
JP7013459B2 (ja) 2016-10-31 2022-01-31 メルク パテント ゲーエムベーハー 有機機能材料の調合物
CN109863223B (zh) 2016-10-31 2023-06-20 默克专利有限公司 有机功能材料的制剂
KR102472751B1 (ko) 2016-12-06 2022-11-30 메르크 파텐트 게엠베하 전자 디바이스의 제조 방법
CN110168047B (zh) 2016-12-13 2023-08-08 默克专利有限公司 有机功能材料的制剂
KR102504432B1 (ko) 2016-12-22 2023-02-27 메르크 파텐트 게엠베하 적어도 2종의 유기-기능성 화합물을 포함하는 혼합물
KR102633478B1 (ko) * 2016-12-23 2024-02-06 솔루스첨단소재 주식회사 유기 화합물 및 이를 이용한 유기 전계 발광 소자
CN108250129B (zh) * 2016-12-29 2021-11-30 中节能万润股份有限公司 一种以二芳基蒽酮为核心的化合物及其在有机电致发光器件上的应用
TWI791481B (zh) 2017-01-30 2023-02-11 德商麥克專利有限公司 形成有機電致發光（ｅｌ）元件之方法
TWI763772B (zh) 2017-01-30 2022-05-11 德商麥克專利有限公司 電子裝置之有機元件的形成方法
JP7123967B2 (ja) 2017-03-31 2022-08-23 メルク パテント ゲーエムベーハー 有機発光ダイオード（ｏｌｅｄ）のための印刷方法
CN110494514A (zh) 2017-04-10 2019-11-22 默克专利有限公司 有机功能材料的制剂
JP7330898B2 (ja) 2017-05-03 2023-08-22 メルク パテント ゲーエムベーハー 有機機能材料の調合物
KR102449219B1 (ko) * 2017-05-17 2022-09-30 삼성디스플레이 주식회사 유기 발광 소자
WO2019016184A1 (fr) 2017-07-18 2019-01-24 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique
CN111418081B (zh) 2017-12-15 2024-09-13 默克专利有限公司 有机功能材料的制剂
GB2569636A (en) * 2017-12-21 2019-06-26 Sumitomo Chemical Co Composition
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JP7247231B2 (ja) 2018-02-26 2023-03-28 メルク パテント ゲーエムベーハー 有機機能材料の調合物
EP3807367B1 (fr) 2018-06-15 2023-07-19 Merck Patent GmbH Formulation d'un matériau fonctionnel organique
KR20210056432A (ko) 2018-09-24 2021-05-18 메르크 파텐트 게엠베하 과립형 재료의 제조 방법
WO2020094538A1 (fr) 2018-11-06 2020-05-14 Merck Patent Gmbh Procédé de formation d'un élément organique d'un dispositif électronique
CN109651340A (zh) * 2018-12-31 2019-04-19 瑞声科技（南京）有限公司 一种双咔唑吡啶化合物及其应用
CN112250585B (zh) * 2019-07-22 2023-11-14 南京高光半导体材料有限公司 一种空穴传输材料及使用该种材料的有机电致发光器件
CN112538022A (zh) * 2019-09-23 2021-03-23 北京大学深圳研究生院 一种新型空穴传输材料及其应用
WO2021213918A1 (fr) 2020-04-21 2021-10-28 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique
EP4139971A1 (fr) 2020-04-21 2023-03-01 Merck Patent GmbH Émulsions comprenant des matériaux fonctionnels organiques
WO2021259824A1 (fr) 2020-06-23 2021-12-30 Merck Patent Gmbh Procédé de production d'un mélange
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WO2022223675A1 (fr) 2021-04-23 2022-10-27 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique
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WO2025032039A1 (fr) 2023-08-07 2025-02-13 Merck Patent Gmbh Procédé de préparation d'un dispositif électronique
CN117886845A (zh) * 2024-01-22 2024-04-16 阜阳欣奕华材料科技有限公司 一种咔唑类化合物、包含其的有机电致发光器件
CN119859149B (zh) * 2025-03-25 2025-09-26 西安瑞联新材料股份有限公司 一种用于有机电致发光器件的螺咪唑类化合物

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5007945A (en) * 1990-04-12 1991-04-16 Air Products And Chemicals, Inc. Membranes formed from aromatic polyarylates
US5176977A (en) * 1991-07-01 1993-01-05 Eastman Kodak Company Nonpolymeric amorphous developer compositions and developing processes
EP0539778A1 (fr) * 1991-11-01 1993-05-05 Sumitomo Chemical Company, Limited Composition pour réserve positive sensible aux rayonnements
US5232471A (en) * 1992-05-13 1993-08-03 Air Products And Chemicals, Inc. Membranes formed from nitrated polyarylates
WO1994004250A1 (fr) * 1992-08-13 1994-03-03 The Dow Chemical Company Separations de gaz a l'aide de membranes polymeres vitreuses a des temperatures inferieures a la temperature ambiante
US5447960A (en) * 1993-10-04 1995-09-05 Dowelanco Fungicidal use of phenolic aromatic compounds
JPH0980791A (ja) * 1995-09-12 1997-03-28 Canon Inc 電子写真感光体、プロセスカートリッジ及び電子写真装置
US5698740A (en) * 1993-10-01 1997-12-16 Toyo Ink Manufacturing Co., Ltd. Hole-transport material
WO1998002379A2 (fr) * 1996-07-15 1998-01-22 The Dow Chemical Company Reacteur et procede de synthese de peroxyde d'hydrogene
JPH1095972A (ja) * 1996-08-02 1998-04-14 Mitsui Petrochem Ind Ltd 有機電界発光素子
JPH11255859A (ja) * 1998-03-13 1999-09-21 Tadao Nakaya ポリウレタン、眼鏡用レンズ材料、コンタクトレンズ材料、レンズ、ポリウレタンの製造方法
US20030162653A1 (en) * 2001-11-05 2003-08-28 Generon Igs, Inc. Two step production of polycarbonates
US20040192848A1 (en) * 2000-11-14 2004-09-30 Ferrania, S.P.A Optical film comprising polyarylates containing bis-(hydroxyphenyl)-fluorene-ortho-disubstituted bisphenols
JP2005085599A (ja) * 2003-09-09 2005-03-31 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子
WO2005053055A1 (fr) * 2003-11-27 2005-06-09 Merck Patent Gmbh Element organique electroluminescent
US20050209404A1 (en) * 2004-02-13 2005-09-22 Fuji Photo Film Co., Ltd. Film and image display device utilizing same
JP2005272614A (ja) * 2004-03-24 2005-10-06 Fuji Photo Film Co Ltd ポリウレタンおよび前記ポリウレタンからなる光学フィルム
WO2006033554A1 (fr) * 2004-09-22 2006-03-30 Lg Chem, Ltd. Film compensateur optique en polyarylate pour affichage a cristaux liquides et son procede de preparation
JP2006089541A (ja) * 2004-09-22 2006-04-06 Fuji Photo Film Co Ltd ポリアリレートおよび前記ポリアリレートからなるフィルム
EP1651013A1 (fr) * 2003-07-08 2006-04-26 Konica Minolta Holdings, Inc. Dispositif electroluminescent organique, dispositif d'illumination et affichage
EP1666970A1 (fr) * 2003-09-18 2006-06-07 Mitsubishi Gas Chemical Company, Inc. Compose pour reserve et composition sensible au rayonnement
JP2007049055A (ja) * 2005-08-12 2007-02-22 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子

Family Cites Families (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
DE4111878A1 (de) 1991-04-11 1992-10-15 Wacker Chemie Gmbh Leiterpolymere mit konjugierten doppelbindungen
US5151629A (en) 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
JP2855066B2 (ja) * 1993-11-25 1999-02-10 三菱電機株式会社 荷電粒子線強度分布測定装置
EP0676461B1 (fr) 1994-04-07 2002-08-14 Covion Organic Semiconductors GmbH Composés spiro et leur application comme matières électroluminescentes
DE4436773A1 (de) 1994-10-14 1996-04-18 Hoechst Ag Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien
WO1997005184A1 (fr) 1995-07-28 1997-02-13 The Dow Chemical Company Fluorenes a substitution 2,7-aryle en position 9, oligomeres et polymeres de fluorenes substitues en position 9
DE19614971A1 (de) 1996-04-17 1997-10-23 Hoechst Ag Polymere mit Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien
DE19652261A1 (de) 1996-12-16 1998-06-18 Hoechst Ag Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen
DE19846766A1 (de) 1998-10-10 2000-04-20 Aventis Res & Tech Gmbh & Co Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften
US6166172A (en) 1999-02-10 2000-12-26 Carnegie Mellon University Method of forming poly-(3-substituted) thiophenes
WO2000070655A2 (fr) 1999-05-13 2000-11-23 The Trustees Of Princeton University Dispositifs electroluminescents organiques a tres haute performance utilisant l'electrophosphorescence
KR100946314B1 (ko) 1999-12-01 2010-03-09 더 트러스티즈 오브 프린스턴 유니버시티 인광성 유기금속화합물을 포함하는 유기 발광 장치
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
CN101924190B (zh) 2000-08-11 2012-07-04 普林斯顿大学理事会 有机金属化合物和发射转换有机电致磷光
JP4154140B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 金属配位化合物
JP4154139B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子
JP4154138B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子、表示装置及び金属配位化合物
DE10207859A1 (de) 2002-02-20 2003-09-04 Univ Dresden Tech Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung
GB0226010D0 (en) 2002-11-08 2002-12-18 Cambridge Display Tech Ltd Polymers for use in organic electroluminescent devices
DE10304819A1 (de) 2003-02-06 2004-08-19 Covion Organic Semiconductors Gmbh Carbazol-enthaltende konjugierte Polymere und Blends, deren Darstellung und Verwendung
DE10314102A1 (de) 2003-03-27 2004-10-14 Covion Organic Semiconductors Gmbh Verfahren zur Herstellung von hochreinen Organo-Iridium-Verbindungen
EP1491568A1 (fr) 2003-06-23 2004-12-29 Covion Organic Semiconductors GmbH Polymères semi-conducteurs
DE10328627A1 (de) 2003-06-26 2005-02-17 Covion Organic Semiconductors Gmbh Neue Materialien für die Elektrolumineszenz
KR101105619B1 (ko) 2003-07-07 2012-01-18 메르크 파텐트 게엠베하 유기 방출형 반도체 및 매트릭스 물질의 혼합물, 이들의용도 및 상기 물질을 함유하는 전자 부품
DE10333232A1 (de) 2003-07-21 2007-10-11 Merck Patent Gmbh Organisches Elektrolumineszenzelement
DE10337346A1 (de) 2003-08-12 2005-03-31 Covion Organic Semiconductors Gmbh Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung
JP2005085588A (ja) 2003-09-08 2005-03-31 Matsushita Electric Works Ltd 調光制御システム
CN1853141A (zh) * 2003-09-18 2006-10-25 三菱瓦斯化学株式会社 抗蚀化合物和辐射敏感组合物
DE10345572A1 (de) 2003-09-29 2005-05-19 Covion Organic Semiconductors Gmbh Metallkomplexe
US7659540B2 (en) 2003-10-22 2010-02-09 Merck Patent Gmbh Materials for electroluminescence and the utilization thereof
DE10357044A1 (de) 2003-12-04 2005-07-14 Novaled Gmbh Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten
DE102004020298A1 (de) 2004-04-26 2005-11-10 Covion Organic Semiconductors Gmbh Elektrolumineszierende Polymere und deren Verwendung
TW200613515A (en) 2004-06-26 2006-05-01 Merck Patent Gmbh Compounds for organic electronic devices
DE102004031000A1 (de) 2004-06-26 2006-01-12 Covion Organic Semiconductors Gmbh Organische Elektrolumineszenzvorrichtungen
DE102004032527A1 (de) 2004-07-06 2006-02-02 Covion Organic Semiconductors Gmbh Elektrolumineszierende Polymere
TW200639140A (en) 2004-12-01 2006-11-16 Merck Patent Gmbh Compounds for organic electronic devices
EP1669386A1 (fr) 2004-12-06 2006-06-14 Covion Organic Semiconductors GmbH Polymères conjugués, leur représentation et utilisation
DE102005023437A1 (de) 2005-05-20 2006-11-30 Merck Patent Gmbh Verbindungen für organische elektronische Vorrichtungen
DE102005037734B4 (de) 2005-08-10 2018-02-08 Merck Patent Gmbh Elektrolumineszierende Polymere, ihre Verwendung und bifunktionelle monomere Verbindungen
DE102005058543A1 (de) 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
DE102005060473A1 (de) 2005-12-17 2007-06-28 Merck Patent Gmbh Konjugierte Polymere, deren Darstellung und Verwendung
DE102006015183A1 (de) 2006-04-01 2007-10-04 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102006025846A1 (de) 2006-06-02 2007-12-06 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102006031990A1 (de) 2006-07-11 2008-01-17 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
JP2009182088A (ja) * 2008-01-30 2009-08-13 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5007945A (en) * 1990-04-12 1991-04-16 Air Products And Chemicals, Inc. Membranes formed from aromatic polyarylates
US5176977A (en) * 1991-07-01 1993-01-05 Eastman Kodak Company Nonpolymeric amorphous developer compositions and developing processes
EP0539778A1 (fr) * 1991-11-01 1993-05-05 Sumitomo Chemical Company, Limited Composition pour réserve positive sensible aux rayonnements
US5232471A (en) * 1992-05-13 1993-08-03 Air Products And Chemicals, Inc. Membranes formed from nitrated polyarylates
WO1994004250A1 (fr) * 1992-08-13 1994-03-03 The Dow Chemical Company Separations de gaz a l'aide de membranes polymeres vitreuses a des temperatures inferieures a la temperature ambiante
US5698740A (en) * 1993-10-01 1997-12-16 Toyo Ink Manufacturing Co., Ltd. Hole-transport material
US5447960A (en) * 1993-10-04 1995-09-05 Dowelanco Fungicidal use of phenolic aromatic compounds
JPH0980791A (ja) * 1995-09-12 1997-03-28 Canon Inc 電子写真感光体、プロセスカートリッジ及び電子写真装置
WO1998002379A2 (fr) * 1996-07-15 1998-01-22 The Dow Chemical Company Reacteur et procede de synthese de peroxyde d'hydrogene
JPH1095972A (ja) * 1996-08-02 1998-04-14 Mitsui Petrochem Ind Ltd 有機電界発光素子
JPH11255859A (ja) * 1998-03-13 1999-09-21 Tadao Nakaya ポリウレタン、眼鏡用レンズ材料、コンタクトレンズ材料、レンズ、ポリウレタンの製造方法
US20040192848A1 (en) * 2000-11-14 2004-09-30 Ferrania, S.P.A Optical film comprising polyarylates containing bis-(hydroxyphenyl)-fluorene-ortho-disubstituted bisphenols
US20030162653A1 (en) * 2001-11-05 2003-08-28 Generon Igs, Inc. Two step production of polycarbonates
EP1651013A1 (fr) * 2003-07-08 2006-04-26 Konica Minolta Holdings, Inc. Dispositif electroluminescent organique, dispositif d'illumination et affichage
JP2005085599A (ja) * 2003-09-09 2005-03-31 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子
EP1666970A1 (fr) * 2003-09-18 2006-06-07 Mitsubishi Gas Chemical Company, Inc. Compose pour reserve et composition sensible au rayonnement
WO2005053055A1 (fr) * 2003-11-27 2005-06-09 Merck Patent Gmbh Element organique electroluminescent
US20050209404A1 (en) * 2004-02-13 2005-09-22 Fuji Photo Film Co., Ltd. Film and image display device utilizing same
JP2005272614A (ja) * 2004-03-24 2005-10-06 Fuji Photo Film Co Ltd ポリウレタンおよび前記ポリウレタンからなる光学フィルム
WO2006033554A1 (fr) * 2004-09-22 2006-03-30 Lg Chem, Ltd. Film compensateur optique en polyarylate pour affichage a cristaux liquides et son procede de preparation
JP2006089541A (ja) * 2004-09-22 2006-04-06 Fuji Photo Film Co Ltd ポリアリレートおよび前記ポリアリレートからなるフィルム
JP2007049055A (ja) * 2005-08-12 2007-02-22 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
D. S. TARBELL, Y. SATO: "The Synthesis of 9-Phenanthrylmethyldichlorophenol and Related Compounds", J. AM. CHEM. SOC., vol. 68, 1946, pages 1091 - 1094, XP002527921 *
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002527926, Database accession no. 8563317 (BRN) *
DATABASE WPI Week 200735, Derwent World Patents Index; AN 2007-366366, XP002527927 *
K. ONO ET AL.: "Synthesis and Properties of 9,9'-Diaryl-4,5-diazafluorenes. A New Type of Electron-Transporting and Hole-Blocking Material in EL Device", CHEMISTRY LETTERS, vol. 33, no. 3, 9 February 2004 (2004-02-09), pages 276 - 277, XP009116781 *
K.-T. LIU ET AL., JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 47, no. 1, 2000, Taipei, TW, pages 71 - 76 *
K.-T. LIU ET AL.: "Solvolysis of 9-aryl-9-chlorofluorenes revisited. Solvent and substituent effect", ORGANIC REACTIVITY, vol. 31, no. 1, 1997, pages 59 - 66, XP009116780 *
K.-T. LIU, Y.-S. LIN: "Solvent and Substituent Effects in the Solvolysis of 9-Aryl-9-bromofluorenes", JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 47, no. 1, 2000, pages 71 - 76, XP009116779 *
M. BALLESTER ET AL.: "Inert Carbon Free Radicals. 5. Perchloro-9-phenylfluorenyl Radical Series", J. ORG. CHEM., vol. 49, no. 5, 1984, pages 770 - 778, XP002527924 *
M. R. PIXTON, D. R. PAUL: "Gas Transport Properties of Polyarylates Part II: Tetrabromination of the Bisphenol", JOURNAL OF POLYMER SCIENCE: PART B: POLYMER PHYSICS, vol. 33, 1995, pages 1353 - 1364, XP002527923 *
N. CHEN ET AL.: "New gas separation membrane materials - halogenated dicarbonyl phenylene based polyarylates", POLYMERIC MATERIALS SCIENCE AND ENGINEERING, vol. 66, 1992, pages 412 - 413, XP009116849 *
R. BOLTON ET AL.: "Competition in Intramolecular Arylation of Triphenylmethanols", J. CHEM. SOC. PERKIN TRANS. II, 1986, pages 405 - 408, XP009116852 *
S. SETAYESH ET AL.: "Polyfluorenes with Polyphenylene Dendron Side Chains: Toward Non-Aggregating, Light-Emitting Polymers", J. AM. CHEM. SOC., vol. 123, no. 5, 16 January 2001 (2001-01-16), pages 946 - 953, XP002527922 *

Cited By (163)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11895917B2 (en) 2008-06-05 2024-02-06 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US10020454B2 (en) 2008-06-05 2018-07-10 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
EP2301926A1 (fr) 2008-06-05 2011-03-30 Idemitsu Kosan Co., Ltd. Composé halogéné, composé polycyclique, et élément électroluminescent organique comprenant le composé polycyclique
CN102056911A (zh) * 2008-06-05 2011-05-11 出光兴产株式会社 卤素化合物、多环系化合物及使用其的有机电致发光元件
US11069862B2 (en) 2008-06-05 2021-07-20 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
CN102056911B (zh) * 2008-06-05 2015-07-22 出光兴产株式会社 卤素化合物、多环系化合物及使用其的有机电致发光元件
US9056870B2 (en) 2008-06-05 2015-06-16 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US9660203B2 (en) 2008-06-05 2017-05-23 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
EP2301926A4 (fr) * 2008-06-05 2012-01-04 Idemitsu Kosan Co Composé halogéné, composé polycyclique, et élément électroluminescent organique comprenant le composé polycyclique
US8927118B2 (en) 2008-06-05 2015-01-06 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US9847493B2 (en) 2008-06-05 2017-12-19 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US10026907B2 (en) 2008-06-05 2018-07-17 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
CN102482279A (zh) * 2009-03-30 2012-05-30 德山金属株式会社 有机电子装置及其化合物与终端机
EP2415773A4 (fr) * 2009-03-30 2013-04-24 Duksan Hi Metal Co Ltd Dispositif électronique organique, composés pour celui-ci et terminal
US9233923B2 (en) 2009-03-30 2016-01-12 Duk San Neolux Co., Ltd. Organic compounds for organic electronic devices and terminals
US20120018717A1 (en) * 2009-03-30 2012-01-26 Duksan High Metal Co., Ltd. Organic electronic device, compounds for same, and terminal
CN102482279B (zh) * 2009-03-30 2015-08-12 德山新勒克斯 有机电子装置及其化合物与终端机
JP2012521418A (ja) * 2009-03-30 2012-09-13 ドゥクサン ハイ メタル カンパニー リミテッド 有機電気素子及びその化合物、端末
WO2010137601A1 (fr) 2009-05-29 2010-12-02 Semiconductor Energy Laboratory Co., Ltd. Dérivé de fluorène, élément émetteur de lumière, dispositif émetteur de lumière, dispositif électronique et dispositif d'éclairage
US9051239B2 (en) 2009-05-29 2015-06-09 Semiconductor Energy Laboratory Co., Ltd. Fluorene derivative, light-emitting element, light-emitting device, electronic device, and lighting device
US9741937B2 (en) 2009-05-29 2017-08-22 Semiconductor Energy Laboratory Co., Ltd. Fluorene derivative, light-emitting element, light-emitting device, electronic device, and lighting device
JP7759983B2 (ja) 2009-05-29 2025-10-24 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、および照明装置
US10862042B2 (en) 2009-05-29 2020-12-08 Semiconductor Energy Laboratory Co., Ltd. Fluorene derivative, light-emitting element, light-emitting device, electronic device, and lighting device
JP2024073634A (ja) * 2009-05-29 2024-05-29 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、および照明装置
US10553797B2 (en) 2009-05-29 2020-02-04 Semiconductor Energy Laboratory Co., Ltd. Fluorene derivative, light-emitting elements, light-emitting device, electronic device, and lighting device
EP2435399A4 (fr) * 2009-05-29 2012-11-14 Semiconductor Energy Lab Dérivé de fluorène, élément émetteur de lumière, dispositif émetteur de lumière, dispositif électronique et dispositif d'éclairage
JP2012531737A (ja) * 2009-06-25 2012-12-10 チェイル インダストリーズ インコーポレイテッド 有機光電子素子用化合物、それを含む有機発光ダイオード、および前記有機発光ダイオードを含む表示装置
US9017827B2 (en) 2009-06-25 2015-04-28 Cheil Industries, Inc. Indenocarbazole compound for optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
WO2011032626A1 (fr) 2009-09-16 2011-03-24 Merck Patent Gmbh Complexes métalliques
US10233159B2 (en) 2009-11-17 2019-03-19 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2011060877A2 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
US9187456B2 (en) 2009-11-17 2015-11-17 Merck Patent Gmbh Materials for organic electroluminescent devices
JP2013510889A (ja) * 2009-11-17 2013-03-28 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
WO2011060859A1 (fr) 2009-11-17 2011-05-26 Merck Patent Gmbh Matériaux pour des dispositifs électroluminescents organiques
DE102009053644B4 (de) 2009-11-17 2019-07-04 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US10981880B2 (en) 2009-11-17 2021-04-20 Merck Patent Gmbh Materials for organic electroluminescent devices
US20160096809A1 (en) * 2009-11-17 2016-04-07 Merck Patent Gmbh Materials for organic electroluminescent devices
US11760734B2 (en) 2009-11-17 2023-09-19 Merck Patent Gmbh Materials for organic electroluminescent devices
DE102009053644A1 (de) 2009-11-17 2011-05-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
WO2011085781A1 (fr) 2010-01-16 2011-07-21 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
DE102010004803A1 (de) 2010-01-16 2011-07-21 Merck Patent GmbH, 64293 Materialien für organische Elektrolumineszenzvorrichtungen
JP2011219517A (ja) * 2010-04-05 2011-11-04 Sumitomo Chemical Co Ltd 金属複合体及びそれに有用な化合物
WO2011126063A1 (fr) * 2010-04-05 2011-10-13 住友化学株式会社 Composites de métal et composé utile pour leur préparation
CN102822230A (zh) * 2010-04-05 2012-12-12 住友化学株式会社 金属复合体及对其调制有用的化合物
WO2011137922A1 (fr) 2010-05-03 2011-11-10 Merck Patent Gmbh Formulations et dispositifs électroniques
WO2011160758A1 (fr) 2010-06-24 2011-12-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
DE102010024897A1 (de) 2010-06-24 2011-12-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
CN103038215A (zh) * 2010-07-30 2013-04-10 保土谷化学工业株式会社 具有茚并咔唑环结构的化合物和有机电致发光器件
US9196837B2 (en) 2010-07-30 2015-11-24 Hodogaya Chemical Co., Ltd. Compound having indenocarbazole ring structure, and organic electroluminescent device
CN106977448A (zh) * 2010-07-30 2017-07-25 保土谷化学工业株式会社 具有茚并咔唑环结构的化合物和有机电致发光器件
CN103038215B (zh) * 2010-07-30 2016-12-07 保土谷化学工业株式会社 具有茚并咔唑环结构的化合物和有机电致发光器件
WO2012014500A1 (fr) * 2010-07-30 2012-02-02 保土谷化学工業株式会社 Composé ayant une structure de noyau indénocarbazole et élément électroluminescent organique
DE102010045405A1 (de) 2010-09-15 2012-03-15 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
WO2012034627A1 (fr) 2010-09-15 2012-03-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR101964475B1 (ko) * 2010-10-14 2019-04-01 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
US9653687B2 (en) 2010-10-14 2017-05-16 Merck Patent Gmbh Materials for organic electroluminescent devices
JP2014506392A (ja) * 2010-10-14 2014-03-13 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
KR20140009184A (ko) * 2010-10-14 2014-01-22 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
KR101531612B1 (ko) * 2010-12-02 2015-06-25 제일모직 주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
US9559309B2 (en) 2010-12-02 2017-01-31 Cheil Industries, Inc. Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode
WO2012074210A3 (fr) * 2010-12-02 2012-07-26 제일모직 주식회사 Composé pour un dispositif opto-électronique organique, élément émetteur de lumière organique le comprenant, et dispositif d'affichage comprenant l'élément émetteur de lumière organique
DE102010054316A1 (de) 2010-12-13 2012-06-14 Merck Patent Gmbh Substituierte Tetraarylbenzole
WO2012079678A1 (fr) 2010-12-13 2012-06-21 Merck Patent Gmbh Tétraarylbenzènes substitués
WO2012089294A1 (fr) * 2010-12-28 2012-07-05 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
JP2014503661A (ja) * 2010-12-28 2014-02-13 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
US9738826B2 (en) 2010-12-28 2017-08-22 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2012110178A1 (fr) 2011-02-14 2012-08-23 Merck Patent Gmbh Dispositif et procédé de traitement de cellules et de tissu cellulaire
WO2012126566A1 (fr) 2011-03-24 2012-09-27 Merck Patent Gmbh Matériaux fonctionnels ioniques organiques
WO2012136296A1 (fr) 2011-04-04 2012-10-11 Merck Patent Gmbh Complexes métalliques
WO2012152366A1 (fr) 2011-05-12 2012-11-15 Merck Patent Gmbh Composés ioniques organiques, compositions et dispositifs électroniques
US9051266B2 (en) 2011-11-01 2015-06-09 Industrial Technology Research Institute Carbazole derivatives and organic light emitting diodes comprising the same
TWI425076B (zh) * 2011-11-01 2014-02-01 Ind Tech Res Inst 咔唑衍生物及包含此衍生物之有機發光二極體
WO2013100464A1 (fr) * 2011-12-29 2013-07-04 제일모직 주식회사 Composé pour un élément optoélectronique organique, élément organique émettant de la lumière le comprenant et dispositif d'affichage comprenant l'élément organique émettant de la lumière
KR101497134B1 (ko) * 2011-12-29 2015-03-02 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
CN104024373A (zh) * 2011-12-30 2014-09-03 第一毛织株式会社 用于有机光电子装置的化合物、包括该化合物的有机发光二极管和包括该有机发光二极管的显示器
CN104024373B (zh) * 2011-12-30 2016-02-03 第一毛织株式会社 用于有机光电子装置的化合物、包括该化合物的有机发光二极管和包括该有机发光二极管的显示器
WO2013100467A1 (fr) * 2011-12-30 2013-07-04 제일모직 주식회사 Composé pour dispositif optoélectronique organique, diode organique émettant de la lumière le comprenant et dispositif d'affichage comprenant une diode organique émettant de la lumière
US10121973B2 (en) 2011-12-30 2018-11-06 Cheil Industries, Inc. Compound for organic optoelectronic device, organic light-emitting diode including same, and display device including organic light-emitting diode
US9768389B2 (en) 2011-12-30 2017-09-19 Cheil Industries, Inc. Compound for optoelectronic device, organic light-emitting diode including same, and display device including organic light-emitting diode
KR101507001B1 (ko) 2011-12-30 2015-03-31 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
WO2013107487A1 (fr) 2012-01-16 2013-07-25 Merck Patent Gmbh Complexes organométalliques
WO2013113349A1 (fr) 2012-01-30 2013-08-08 Merck Patent Gmbh Nanocristaux sur fibres
EP3101088A1 (fr) 2012-02-14 2016-12-07 Merck Patent GmbH Matériaux pour dispositif électroluminescent organique
EP3235892A1 (fr) 2012-02-14 2017-10-25 Merck Patent GmbH Matériaux pour dispositif électroluminescent organique
WO2013120577A1 (fr) 2012-02-14 2013-08-22 Merck Patent Gmbh Composés de spirobifluorène pour dispositifs organiques électroluminescents
WO2014023388A1 (fr) 2012-08-10 2014-02-13 Merck Patent Gmbh Matériaux pour dispositifs organiques à électroluminescence
WO2014079532A1 (fr) 2012-11-20 2014-05-30 Merck Patent Gmbh Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques
WO2015135625A1 (fr) 2014-03-13 2015-09-17 Merck Patent Gmbh Formulations de composés luminescents
WO2015197156A1 (fr) 2014-06-25 2015-12-30 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2016184540A1 (fr) 2015-05-18 2016-11-24 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2017012687A1 (fr) 2015-07-22 2017-01-26 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
EP4236652A2 (fr) 2015-07-29 2023-08-30 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
WO2017194435A1 (fr) 2016-05-11 2017-11-16 Merck Patent Gmbh Compositions pour cellules électrochimiques
EP3978477A2 (fr) 2016-06-03 2022-04-06 Merck Patent GmbH Matériaux pour dispositif électroluminescent organique
WO2017207596A1 (fr) 2016-06-03 2017-12-07 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018104194A1 (fr) 2016-12-05 2018-06-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018104193A1 (fr) 2016-12-05 2018-06-14 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018127465A1 (fr) 2017-01-04 2018-07-12 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018138306A1 (fr) 2017-01-30 2018-08-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2018149769A1 (fr) 2017-02-14 2018-08-23 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2019081391A1 (fr) 2017-10-24 2019-05-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2019145316A1 (fr) 2018-01-25 2019-08-01 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2019233904A1 (fr) 2018-06-07 2019-12-12 Merck Patent Gmbh Dispositifs electroluminescents organiques
WO2020011686A1 (fr) 2018-07-09 2020-01-16 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2020094542A1 (fr) 2018-11-06 2020-05-14 Merck Patent Gmbh Dérivés de 5,6-diphényl-5,6-dihydro-dibenzo[c,e][1,2]azaphosphorine et de 6-phényl-6h-dibenzo[c,e][1,2]thiazine-5,5-dioxyde et composés similaires en tant que matériaux organiques d'électroluminescence pour des oled
WO2020099307A1 (fr) 2018-11-15 2020-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2020127165A1 (fr) 2018-12-19 2020-06-25 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
WO2020148303A1 (fr) 2019-01-17 2020-07-23 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US12279521B2 (en) * 2019-01-17 2025-04-15 Merck Patent Gmbh Materials for organic electroluminescent devices
US20220140245A1 (en) * 2019-01-17 2022-05-05 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2021043755A1 (fr) 2019-09-03 2021-03-11 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2021078831A1 (fr) 2019-10-25 2021-04-29 Merck Patent Gmbh Composés pouvant être utilisés dans un dispositif électronique organique
WO2021122538A1 (fr) 2019-12-18 2021-06-24 Merck Patent Gmbh Composés aromatiques pour dispositifs électroluminescents organiques
WO2021122740A1 (fr) 2019-12-19 2021-06-24 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
WO2021151922A1 (fr) 2020-01-29 2021-08-05 Merck Patent Gmbh Dérivés de benzimidazole
WO2021170522A1 (fr) 2020-02-25 2021-09-02 Merck Patent Gmbh Utilisation de composés hétérocycliques dans un dispositif électronique organique
WO2021175706A1 (fr) 2020-03-02 2021-09-10 Merck Patent Gmbh Utilisation de composés sulfone dans un dispositif électronique organique
WO2021185712A1 (fr) 2020-03-17 2021-09-23 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques
WO2021185829A1 (fr) 2020-03-17 2021-09-23 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2021191183A1 (fr) 2020-03-26 2021-09-30 Merck Patent Gmbh Composés cycliques pour dispositifs électroluminescents organiques
WO2021204646A1 (fr) 2020-04-06 2021-10-14 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
WO2022002771A1 (fr) 2020-06-29 2022-01-06 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022002772A1 (fr) 2020-06-29 2022-01-06 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques
WO2022069422A1 (fr) 2020-09-30 2022-04-07 Merck Patent Gmbh Composés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques
WO2022069421A1 (fr) 2020-09-30 2022-04-07 Merck Patent Gmbh Composés pouvant être utilisés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques
WO2022079068A1 (fr) 2020-10-16 2022-04-21 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022079067A1 (fr) 2020-10-16 2022-04-21 Merck Patent Gmbh Composés comprenant des hétéroatomes pour dispositifs électroluminescents organiques
WO2022101171A1 (fr) 2020-11-10 2022-05-19 Merck Patent Gmbh Composés sulfureux pour dispositifs électroluminescents organiques
WO2022117473A1 (fr) 2020-12-02 2022-06-09 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022129116A1 (fr) 2020-12-18 2022-06-23 Merck Patent Gmbh Dérivés d'indolo[3.2.1-jk]carbazole-6-carbonitrile utilisés en tant qu'émetteurs fluorescents bleus destinés à être utilisés dans des oled
EP4676208A2 (fr) 2020-12-18 2026-01-07 Merck Patent GmbH Hétéro-aromates azotés pour dispositifs électroluminescents organiques
WO2022129113A1 (fr) 2020-12-18 2022-06-23 Merck Patent Gmbh Composés hétéroaromatiques azotés pour dispositifs électroluminescents organiques
WO2022129114A1 (fr) 2020-12-18 2022-06-23 Merck Patent Gmbh Composés azotés pour dispositifs électroluminescents organiques
WO2022157343A1 (fr) 2021-01-25 2022-07-28 Merck Patent Gmbh Composés azotés pour dispositifs électroluminescents organiques
WO2022184601A1 (fr) 2021-03-02 2022-09-09 Merck Patent Gmbh Composés pour dispositifs électroluminescents organiques
WO2022194799A1 (fr) 2021-03-18 2022-09-22 Merck Patent Gmbh Composés hétéroaromatiques pour dispositifs électroluminescents organiques
WO2022229234A1 (fr) 2021-04-30 2022-11-03 Merck Patent Gmbh Composés hétérocycliques azotés pour dispositifs électroluminescents organiques
WO2023041454A1 (fr) 2021-09-14 2023-03-23 Merck Patent Gmbh Composés hétérocycliques contenant du bore pour dispositifs électroluminescents organiques
WO2023072799A1 (fr) 2021-10-27 2023-05-04 Merck Patent Gmbh Composés hétérocycliques contenant du bore et de l'azote pour dispositifs électroluminescents organiques
WO2023117835A1 (fr) 2021-12-21 2023-06-29 Merck Patent Gmbh Dispositifs électroniques
WO2023117836A1 (fr) 2021-12-21 2023-06-29 Merck Patent Gmbh Dispositifs électroniques
WO2023161168A1 (fr) 2022-02-23 2023-08-31 Merck Patent Gmbh Hétérocycles aromatiques pour dispositifs électroluminescents organiques
WO2023161167A1 (fr) 2022-02-23 2023-08-31 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2023208899A1 (fr) 2022-04-28 2023-11-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2023213837A1 (fr) 2022-05-06 2023-11-09 Merck Patent Gmbh Composés cycliques pour dispositifs électroluminescents organiques
WO2023247345A1 (fr) 2022-06-20 2023-12-28 Merck Patent Gmbh Hétérocycles pour dispositifs photoélectriques
WO2023247338A1 (fr) 2022-06-20 2023-12-28 Merck Patent Gmbh Hétérocycles organiques pour dispositifs photoélectriques
WO2024061942A1 (fr) 2022-09-22 2024-03-28 Merck Patent Gmbh Composés contenant de l'azote pour dispositifs électroluminescents organiques
WO2024061948A1 (fr) 2022-09-22 2024-03-28 Merck Patent Gmbh Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques
WO2024094592A2 (fr) 2022-11-01 2024-05-10 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2024149694A1 (fr) 2023-01-10 2024-07-18 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2024153568A1 (fr) 2023-01-17 2024-07-25 Merck Patent Gmbh Hétérocycles pour dispositifs électroluminescents organiques
WO2024184050A1 (fr) 2023-03-07 2024-09-12 Merck Patent Gmbh Composés azotés cycliques pour dispositifs électroluminescents organiques
WO2025003084A1 (fr) 2023-06-28 2025-01-02 Merck Patent Gmbh Composés dicyanoaryle pour dispositifs électroluminescents organiques
EP4486099A1 (fr) 2023-06-30 2025-01-01 Merck Patent GmbH Composés pour dispositifs électroluminescents organiques
WO2025045935A1 (fr) 2023-08-31 2025-03-06 Merck Patent Gmbh Composés aromatiques contenant des groupes cyano pour dispositifs électroluminescents organiques
WO2025109056A1 (fr) 2023-11-24 2025-05-30 Merck Patent Gmbh Hétérocycles contenant de l'oxygène pour dispositifs électroluminescents organiques
WO2025132194A1 (fr) 2023-12-20 2025-06-26 Merck Patent Gmbh Nouveaux matériaux pour dispositifs électroluminescents organiques
WO2025181044A1 (fr) 2024-02-29 2025-09-04 Merck Patent Gmbh Composés contenant de l'azote pour dispositifs électroluminescents organiques
WO2025181097A1 (fr) 2024-02-29 2025-09-04 Merck Patent Gmbh Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques
WO2025181124A1 (fr) 2024-03-01 2025-09-04 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2026008276A1 (fr) 2024-07-04 2026-01-08 Merck Patent Gmbh Matériaux pour diodes électroluminescentes organiques
WO2026008275A1 (fr) 2024-07-04 2026-01-08 Merck Patent Gmbh Matériaux pour diodes électroluminescentes organiques

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CN105906546B (zh) 2019-02-22
CN104327003A (zh) 2015-02-04
CN105906546A (zh) 2016-08-31
JP2011521894A (ja) 2011-07-28
TW201004904A (en) 2010-02-01
KR101578570B1 (ko) 2015-12-28
JP5653902B2 (ja) 2015-01-14
CN104327003B (zh) 2017-10-24
US20110037027A1 (en) 2011-02-17
US8361638B2 (en) 2013-01-29
CN101983190A (zh) 2011-03-02
ATE555092T1 (de) 2012-05-15
DE102008017591A1 (de) 2009-10-08
KR20100133467A (ko) 2010-12-21
EP2260023A1 (fr) 2010-12-15
EP2260023B1 (fr) 2012-04-25

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